Ankle boots and booties are two types of shoes that many women own and may desire to own. Ankle boots typically end slightly above the ankles and booties end right at or below the ankle. Nevertheless, both types of shoes have become very trendy as of late. We're going to focus on making sure that the ankle boots that you wear are style, age, and outfit appropriate. Don't you just cringe at the sight of a woman traipsing around in fluffy ankle boots, leggings, and a velour hoodie? Or what about the lady who is stuck in the 1800s in a plaid a-line skirt and Laura Ingalls Wilder round toe ankle boots? It's time to venture into the 21st century; make sure your shoe wardrobe is up to date by following our ankle boot guide. Ankle Boots vs. Booties: The Practicality Struggle Booties are most definitely the cuter and trendier of the two shoes, but not as practical. Booties typically come in sky high heels and may not be practical in the snow, or for a mom lugging around a 15 pound child in her arms. In regards to practicality, ankle boots win. Ankle boots can be worn by most women. Yes, ankle boots also have flat soles. These Mazzey ankle boots by Jessica Simpson are fashionably practical. The slouch boot has a cableknit overlay and a sturdy modest heel. These ankle boots can be paired with pencil jeans, a denim skirt, or a lovely knit dress. The Dansko Tiffany ankle boots are modest and appropriate for work and any lady who scoffs at the idea of a skyscraper heel. The shoes are comfortable, smooth, and modern. Ugg Ankle Boots Uggs are comfortable, but many a lady has adulterated the classic Ugg boot by appearing sloppily dressed and homely in the comfort boot. You heard it here: Uggs can be worn tastefully. Have you ever explored the Ugg brand? We suggest that you do so and quickly! The Ugg Bellvue ankle boot is waterproof, sturdy, comfortable, and lovely sheepskin. The Bellvue is rugged yet trendy. Pair these boots with jeans, a leather jacket, and thick tights for a perfect look. Also note that these boots can be worn two ways: with the sheepskin rolled down or up. More Fashion Forward Ankle Boots Born Trotters Bogs Steve Madden MIA Ankle Boot Dos and Don'ts Avoid skirts that fall only slightly above the ankle boots. This is a matronly look that flatters no one. Avoid pencil skirts with ankle boots. Ankle boots tends to be bulkier, and booties are best worn with pencil skirts. Do wear tights. Do wear long skirts. Style example: straight, long wool high waist skirt, wide patent belt, patent ankle boots, and ruffle blouse. Consider the event; Ugg boots are inappropriate for church. Ankle boots in general are no good for a wedding.